Horner–Wadsworth–Emmons reaction
Variation on the Wittig chemical reaction / From Wikipedia, the free encyclopedia
Dear Wikiwand AI, let's keep it short by simply answering these key questions:
Can you list the top facts and stats about Horner–Wadsworth–Emmons reaction?
Summarize this article for a 10 year old
The Horner–Wadsworth–Emmons (HWE) reaction is a chemical reaction used in organic chemistry of stabilized phosphonate carbanions with aldehydes (or ketones) to produce predominantly E-alkenes.[1]
Horner–Wadsworth–Emmons reaction | |
---|---|
Named after | Leopold Horner William S. Wadsworth William D. Emmons |
Reaction type | Coupling reaction |
Identifiers | |
Organic Chemistry Portal | wittig-horner-reaction |
RSC ontology ID | RXNO:0000056 |
In 1958, Leopold Horner published a modified Wittig reaction using phosphonate-stabilized carbanions.[2][3] William S. Wadsworth and William D. Emmons further defined the reaction.[4][5]
In contrast to phosphonium ylides used in the Wittig reaction, phosphonate-stabilized carbanions are more nucleophilic but less basic. Likewise, phosphonate-stabilized carbanions can be alkylated. Unlike phosphonium ylides, the dialkylphosphate salt byproduct is easily removed by aqueous extraction.